Colorimetric Transition of Polydiacetylene/Cyclodextrin Supramolecular Assemblies and Implications as Colorimetric Sensors for Food Phenolic Antioxidants

Author:

Sergi Riccardo1,Brugnoli Benedetta1,Sturabotti Elisa1,Piozzi Antonella1,Galantini Luciano1,Taresco Vincenzo2,Francolini Iolanda1ORCID

Affiliation:

1. Department of Chemistry Sapienza University of Rome P.le A. Moro Rome 5–00185 Italy

2. School of Chemistry The University of Nottingham Nottingham NG7 2RD UK

Abstract

AbstractMolecular self‐assembly has significant potential in the field of sensing. Polydiacetylenes (PDAs) are conjugated polymers possessing peculiar optical properties obtained by photopolymerization of self‐assembled diacetylene monomers. Herein, the blue‐to‐red phase transition upon either thermal stimulus or interaction with cyclodextrins (CDs) of two PDAs, bearing either carboxylic (PCDA) or amino (PCDA‐NH2) polar heads, is investigated to develop a colorimetric sensor for food phenolic antioxidants. The change in the PDA polar head does not affect significantly thermo‐chromatic transition. Upon thermal stimulus, in both PDAs, color transition occurs straightforward between two distinct stable states and does not involve the disordering of the PDA crystal phase, as revealed by UV–vis spectroscopy and SAXS analysis. Contrarily, PDA/α‐CD interaction is influenced by intermolecular forces among PDA polar heads and is more efficient for PCDA. α‐CDs presumably cause changes in both PDA backbone conformation and local environment surrounding the individual PDA chains. The PCDA/α‐CD assemblies are investigated as colorimetric sensors for the detection of Tyrosol (Ty) and caffeic acid (CAF), by using the principle of competitive inclusion complex formation. The system results to be more sensitive to CAF than Ty and may permit the determination of CAF in concentration ranges suitable for different food products.

Publisher

Wiley

Subject

Materials Chemistry,Organic Chemistry,Polymers and Plastics,Physical and Theoretical Chemistry,Condensed Matter Physics

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